As mentioned earlier, first step is to make sure the charge holes of the cylinder are all clean. If they are not nice and shiny, brush with a bronze cleaning brush. Another method is to take some of the copper strands from a Chore Boy cleaning pad and wrap these around a old worn brush. Chuck the brush up in a electric drill and use it to clean/polish the inside of each charge hole on the cylinder. It is possible that there is some build up in the cylinder from shooting .38 Special ammo. If so, the above method will get it out. Using a little Hoppes No. 9 will make things work better.
After cleaning the cylinder, see if your reloaded ammunition will chamber. If so, cool. If not, it's time for a little comparison. Take a loaded factory round and compare it to your reloaded ammunition. Use a caliper to measure the diameter of your round and compare it to the factory round measuring at the bullet, immediately behind the crimp, about midway of the body of the case and just in front of the rim. There is the possibility that your dies are not sizing the body of the fired casing down enough to all it to easily chamber. As stated above, there is the possibility that there is a problem with an odd sized bullet or brass that needs trimming.
Occasionally I've had problems chambering a round of .357 Magnum ammunition. It almost always ended up being the result of a build up of grease residue in the charge holes that resulted from having fired a lot of .38 Special ammunition. HTH. Sincerely. brucev.